Molly K. Jenkins is first visualized by the gang as a fat man through Marshall's stories to the gang. He describes her in a variety of compromising yet entertaining situations: peeing out of a moving car window, stripping on a table and throwing Marshall her shirt, provocatively dancing behind an aged corporate banker at GNB during a meeting, and eating an entire jar of Maraschino cherries. Barney, working at GNB, already knows Jenkins is a female and sets out to sleep with her. Ted finds out at Marshall's college bar who Jenkins really is when she shows up to hang out with Marshall, Ted, and Barney. Lily meets Jenkins in person when she unexpectedly goes to GNB to have lunch with Marshall and runs into her in the process.

Shortly after joining the company and getting assigned to work with Marshall, she becomes attracted to him based on several connections the two hold: their shared support for the Vikings, hailing from the same area, Marshall's uncle supposedly haunting a barn in her hometown of Pelican Rapids, and their joint admiration of the gentleman's sport of Skeeball, where Marshall reigns as champion under the title Big Fudge. Marshall is oblivious to the attraction but Ted seems to understand.

One day, Jenkins suddenly kisses Marshall at work. After apologizing, she also expresses remorse for having slept with him in the dark in the company mail room, but Marshall reveals this wasn't him. She cites the Robin Scherbatsky drinking game (But...umm) for her lack of judgement.

As shocked and disappointed Marshall is by the incident, he is more concerned about the fact that Lily feels she is the settler in their relationship, insinuating women don't reach for Marshall. Following their disagreement on the matter, Lily thinks Marshall made up the Jenkins kissing story to settle the feud. Marshall convinces Jenkins to explain to Lily what happened as he thinks it will settle the reacher-settler dispute when in reality Jenkins simply wishes to express remorse for any wrongdoing.

Later at the bar Lily is told by Jenkins that she kissed Marshall, whereupon Lily takes off her jacket, scarf, and jewellery, punches her in the face, and proceeds to beat her senseless. Whether she still works at GNB after that is unknown.

1. Marshall (Co-Worker/Ex-Crush): The two are co-workers in the legal department and routinely hang out until Jenkins is revealed to be a woman to the group and subsequently kisses Marshall, prompting a physical response from Lily.

2. Lily (Enemy): Meets Jenkins while visiting Marshall for lunch at GNB. In the past she assumed the Jenkins in Marshall's entertaining stories was a man. She at first doesn't believe Marshall when he says Jenkins kissed her but then proceeds to beat Jenkins senseless after Jenkins' confession.

4. Robin (Brief Interaction/Possible Friend): Robin and Ted explain the reacher settler theory to Marshall, and using this knowledge he begins a dispute with Lily which inevitably draws in Jenkins.

5. Barney (Possible one-night stand): At the college bar, Barney reveals his intention to sleep with Jenkins to Marshall and Ted. According to the tenets of Stinsonian logic, if Barney made clear to the gang he wished to 'bang' Jenkins and we rely on the fundamental assumption Barney Stinson 'always gets the yes,' Barney may have very well been the guy Jenkins slept with in the mail room. Furthermore, a man of such sexual stature, Barney would have assumed a stance of modesty following the incident, explaining why he did not spread news of his conquest to the gang.